Five years ago this month the influential comedy website Funny or Die took a few baby steps and uploaded its first video, a rough, hastily assembled sketch that starred, appropriately enough, a baby. Pearl McKay was 2 years old at the time, the daughter of parents deeply rooted in Chicago — her mother, Shira Piven, grew up in Evanston, the sister of actor Jeremy Piven. Pearl's father, Adam McKay, got his start in the Chicago comedy scene in the early '90s, then left in 1995 to become a writer at "Saturday Night Live." The video was called "The Landlord" and featured Pearl screaming at McKay's comedy partner, Will Ferrell. Back then, expectations for Funny or Die, which seemed like just another mingling of originally produced comedy videos and user-uploaded material, fell somewhere in line with scores of other, similar Hollywood-Internet hybrid misfires — remember Dot Comedy (NBC), Pop (Steven Spielberg) and SuperDeluxe (TBS)?

Five years later, Funny or Die, which McKay, Ferrell and "Entourage"executive producer Chris Henchy founded on a whim (and with the friendly urging of a venture capital firm), is way beyond baby steps. You might say, to keep the metaphor going, it already has graduated and become a media mogul: This fall there will be four Funny or Die-branded TV shows, two Web series and a movie in production, said CEO Dick Glover. It recently launched an iPad magazine, announced a deal to provide some of the in-flight entertainment for Virgin Airlines and started a commercial division. It's become the place where stars and corporations alike go to seem a little subversive. "The Landlord," the most-watched video in FoD history, has been viewed more than 80 million times, and the site gets 17 million visitors a month. Glover, who said Funny or Die became profitable in late 2010, has not ruled out the possibility ("someday, just not right now") of an initial public offering for Funny or Die stock.

McKay, currently prepping "Anchorman 2" (set in the late '70s, during the transition from traditional newscasts to the 24-7 cable universe, he teased), took time out recently to talk by phone about the site's evolution since 2007. The following is an edited version of a longer conversation.

Q: When you first started in comedy, moving from Philadelphia to Chicago in 1990, going through Second City and iO and co-founding the Upright Citizens Brigade, were you making short videos back then?

A:Yes! And there was no place to put them. There was no outlet. We made them anyway. It was like an animal instinct. A group of us stuck together, Matt Besser, Horatio Sanz, Ian Roberts. It was as if everyone's collective (subconscious) knew the Internet was coming. We would show them in the lobby before (UCB) shows. The first video was about a bunch of us coming back from a party. We were in a car, which speaks to how little we knew what we were doing — shooting in cars is the worst. One of us kept doing a Jack Nicholson impression, then kept doing it, until we're like, "Hey, really, stop it." That turns into a fight.

Q: Later, at "Saturday Night Live," you brought short films back in the 1990s, which had been this marginal thing at "SNL," though the tradition went back to the first season. Sounds like you really wanted to direct.

A: Actually, it went exactly like that! I was going to quit the show. I had been head writer for a couple of years and there was all this stuff I wanted to try, but ultimately it's (Lorne Michaels') show and I should politely move on. My manager said, "If you're going to quit, make an unreasonable demand. What would you want in your dream world?" I didn't want to go to production meetings. I didn't want to be in the room for the actual show any more, which is actually no fun. I wanted a raise. I wanted a budget for short films. And I wanted to name my own screen credit. Lorne said yes. So for the last two years I was there, I was "coordinator of falconry." That was my actual screen credit. Wow, some people were (ticked off)! I'm like, "Relax, this is a comedy show."

Q: You did a short, "The H Is O," where Will Ferrell plays Glenn Frey and sexually harasses Ben Stiller.

A: To this day, I bump into people who whisper, "Hey, the H is O." (As in, "The heat is on.") It's like a secret club. And that was also kind of intentional. I never strove to make those shorts popular. It was more like I was going to film school. I had a crew. I had a budget. I shot 16 mm. I was shooting digital by the second year of this. I made a dozen films all together. I wouldn't have known how to direct "Anchorman" if I hadn't shot those videos. But also, some of them were just too crazy for the format. They were not as populist as what the guys at Lonely Island (Andy Samberg and Co.) are doing on the show now. Those guys grew up making shorts, like a lot of people we hire at Funny or Die. Digital is fluid to them — it's a second language.

Q: Still, you didn't want to do Funny or Die at first, right?

A:I didn't. Ferrell and I still had the dot-com collapse in our heads. The hype around it had gotten so dumb. But the guy who brought the idea to us, Mark Kvamme (of the venture capital firm Sequoia Capital), he had already adjusted. He knew you didn't launch a site like this the way you might have in 1998. It boiled down to, what do we have to lose? None of us, me or Will or Chris, put our money into it. Worst-case scenario, we have an outlet for the stuff we did on "SNL" and it gets 50,000 hits a month. If it was a failure, it wouldn't be a hyped failure. Which is what resonated. It was clearly for the fun of it, and people liked the spontaneity of it.

Q: So "The Landlord" was as roughly made as it looks?

A: Completely. My daughter was going through that phase where she repeated anything you said. My wife would speak French to her, and she would repeat it. I would say "postlapsarian epistemological" and she would repeat it. I said, "You know, Ferrell, Pearl can say anything." So we showed up at his house. My buddy, Drew Antzis, who shot it, was a masseuse at the time. I know him from Chicago, from iO. He said, "I have a couple of massages scheduled. Between them, let's do it." Pearl couldn't focus, but with "Uncle Will," she calmed down. It took about 40 minutes. We didn't think much of it, beyond it being funny. We threw it on the site with no announcement, no press release. Will and I forwarded it to friends. That was about it. Within days, Ellen DeGeneres wanted Pearl on her show. It blew up faster than anything we'd ever done.

Q: Early on, within months of launch, the site also began making corporate-sponsored comedy videos. Weren't you leery of that, that it might change this scrappy, spontaneous thing into something deliberate?

A:We were worried. We talked about that at great length. We decided we would just separate those from the rest, the way Second City had done when it started a business unit. With a firewall, it should be fine. The rule is, never do a video unless there's a chance to do something interesting. When this arrangement works best, it's close to TV, working with advertisers behind you. The best example is Zach Galifianakis' "Between Two Ferns" series. There's corporate money behind it. That hasn't affected the drive of it at all.

Q: But co-opting can be subtle.

A: It can, and we live in a corporate society. Depending on your belief system, that's a positive, a negative or somewhere in between. I'm somewhere in between. Friends give me a hard time about the pants I'm wearing, which are made in China. Well, how do you find the right clothes? Or the right movie studio? The right people giving you checks? Good luck doing the right thing all the time. Will and I discussed this early on: What if Exxon wants an ad? Or Wal-Mart? You have to cater a little.Wal-Martis the biggest distributor of DVDs out there, but personally, I think their manufacturing policies have destroyed our economy and they don't pay their employees enough. I have massive problems with them. At the end of the day, the answer might be that as long as you don't feel a sick feeling in your stomach, you're clean.

Q: Yet the more ubiquitous the Funny or Die brand gets, don't the jokes have to get broader, too?

A: That's really complicated. "Seinfeld," for instance, was a very specific show, and it had a strong point of view and was as popular as any sitcom in history. Stuff that tries to appeal to a lot of people is often white noise and forgettable. Our marching orders are: Keep it as specific to what you think is funny as you like. But it has to be about what is going on in the world. Not politics necessarily. It has to feel relevant. When I was at "SNL," I would constantly get in arguments, "Why aren't we more political? We're not going after Bush." Then look what happened — that Sarah Palin season, they were on fire. It was about something. When we had Paris Hilton respond to John McCain (on Funny or Die), that's when I felt our site working.

Q: Would you let the McCain campaign respond back?

A:They did, just not in a video. Which is when I knew they were desperate. But the door would have been open for McCain to post a video — just like it is for Romney to make fun of himself as an uptight white guy.

Q: But you're a political person. You would do a video with someone even if you didn't like their politics?

A: Maybe we would do something. It would have to poke fun, and they couldn't state policy or anything.

Q: One hallmark of Funny or Die is famous people making fun of themselves. At what point, when everyone is in on a joke, does complicity blunt the edge? You mentioned Palin on “SNL.” Having her in on the joke, aren’t you telling an audience this is just good fun, even if it’s not? Humor often starts with anger.

A: That’s a great point. There’s a false equivalency in this country, a sense that both (political parties) are full of it. That’s not true. When you’ve started a war on false evidence and 500,000 people die as a result, that’s an evil deal: So if Dick Cheney is willing poke fun at himself on Funny or Die, should we let him on?

Q: Was he?

A: You know what ... kind of. This is fantastic: Darrell Hammond was going to do a video because he does a good Dick Cheney, and he knows Dick Cheney, so there was discussion (from Hammond) of ‘I can get Cheney.’ We had a big discussion and here’s what we said: Unless he lets us write and call him out on some of the stuff he’s done, we won’t do it. Those were the terms. We won’t let him come and have happy, fun times then leave it at that. So, you’re right — this is extremely tricky ground for us. As it was for “Saturday Night Live” with Sarah Palin. Which I didn’t like, by the way. We don’t want to be accused of censoring (Funny or Die). We’re open to allowing people to upload pro-right wing videos. But … I guess it comes to personal choice, and I could never stomach Dick Cheney on our site just acting self-deprecating.

Q: This isn’t the same thing, obviously, but you’ve made videos with Lindsay Lohan—

A: Because I don’t care as much. The thing is, with someone like that: Are they in the final stages of a crippling addiction? Seemingly about to die? We had this conversation about Charlie Sheen, who made a cooking show video with us in the middle of all his craziness. It seemed like he could die, didn’t it? He seemed to be going through some psychosis. We talked about whether we should have him and ultimately, someone from the site sat with him and said this guy isn’t going to die — he’s a little wackadoo, but not bad.

Q: Still, you could be enabling him.

A: Yes, that’s right. At “Saturday Night Live,” when we had Chris Farley host, that came up. It was tricky because he was a friend to everyone there and a lot of people were saying “If he is going to get back on his feet, it will come from working and being around people who care for him.” The other side of the argument was, “He’s pretty bad and on a lot of drugs.” And he ended up dying soon after he hosted. Lindsay Lohan? When we shot that, she seemed in a party-girl-getting-in-trouble stage. Dick Cheney? I just don’t know.